US4631085A - Aqueous ink composition for ink-jet recording - Google Patents
Aqueous ink composition for ink-jet recording Download PDFInfo
- Publication number
- US4631085A US4631085A US06/790,197 US79019785A US4631085A US 4631085 A US4631085 A US 4631085A US 79019785 A US79019785 A US 79019785A US 4631085 A US4631085 A US 4631085A
- Authority
- US
- United States
- Prior art keywords
- group
- ink composition
- jet recording
- ink
- aqueous ink
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Definitions
- the present invention relates to an aqueous ink composition suitable for use as printing ink. More particularly, it relates to an aqueous ink composition for ink-jet recording, which is capable of yielding printed images with high quality (i.e., high clearness and sharpness, etc.), and which is also capable of providing stable ink ejection, without causing the plugging of the nozzles of the ink-jet recording apparatus, even if it is used continuously for a long period of time or if it is used intermittently after a period of non-use of the ink-jet recording apparatus.
- high quality i.e., high clearness and sharpness, etc.
- an aqueous ink comprises as the main components a dye, water and a humectant.
- an aqueous ink for use in ink-jet recording should satisfy the following conditions in order to yield an excellent print:
- the ink in order that the ink be compatible with ink droplet formation and control of the direction of the ejected ink droplet streams, it is necessary that its viscosity, surface tension, specific electric conductivity, and density each fall within certain appropriate ranges.
- the ink provide adequately high contrast, clearness and the desired color in the printed image, in particular, for use with full-color printers.
- the ink for ink-jet recording be such that the printed images are resistant to water, light and physical wear.
- the object of the present invention is to provide an aqueous ink composition for ink-jet recording completely satisfying the above outlined conditions. That is to say, the object of the present invention is to provide an aqueous ink composition for ink-jet printing which does not result in plugging of the nozzles, does not change in quality or separate precipitates therefrom with time during storage, but exhibits excellent ink-ejection stability, and has good ink ejection response, shows slight changes in physical properties, if any, when used for a long period with continuous recirculation, or when used intermittently, and, yields printed images which are non-spreading, and have high sharpness and high image density.
- an aqueous ink composition comprising an aqueous solution of a water-soluble dye having the following formula and a humectant dissolved in water, if necessary with addition of other additives thereto: ##STR3## wherein R 1 represents ##STR4## wherein R 4 represents an alkyl group or a hydroxyalkyl group; R 2 represents hydrogen, an alkyl group, an acetyl group, an unsubstituted or substituted benzoyl group, an unsubstituted or substituted benzenesulfonyl group, or a substituted 1,3,5-triazine ring; R 3 represents hydrogen, an alkyl group, an alkoxy group, halogen or a sulfonic acid group; M represents hydrogen ion, an alkali metal cation such as Li + , Na + and K + , amine cation or an ammonium ion; and n is an integer of 1, 2 or 3.
- An aqueous ink composition according to the present invention comprises a water-soluble dye of the above described formula, water and a humectant.
- the above dyes can be prepared by a conventional method.
- the dye (1) given in Table 1 which is a red water-soluble dye, can be prepared as follows: One mole of 4-nitrobenzoyl chloride is allowed to react with 2 moles of morpholine in dioxane at a temperature below room temperature, so that 4-nitrobenzoylmorpholine (m.p. 108° 109° C.) is obtained. The thus obtained nitro compound is reduced in the presence of a 5%Pd-C catalyst to produce 4-aminobenzoylmorpholine.
- the dye be contained in an amount of 0.1 to 20 parts by weight, more preferably 0.5 to 6 parts by weight, with respect to 100 parts by weight of the ink composition in order to obtain high printing quality.
- the humectant for use in the present invention which is employed together with water, is for adjusting the physical properties of the ink composition so as to have the desired properties, to control the drying speed of the ink composition and to increase the solubility of the dye employed in the solvent of the ink composition.
- humectants for use in the aqueous ink according to the present invention are polyhydric alcohols, alkyl ethers of polyhydric alcohols, amine derivatives such as triethanol amine, amides such as dimethylformamide, and nitrogen-containing heterocyclic compounds such as N-methyl-2-pyrrolidone, 2-pyrrolidone and 1,3-dimethyl imidazolidinone.
- polyhydric alcohols are ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol and glycerin.
- alkyl ethers of polyhydric alcohols are ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether and triethylene glycol monoethyl ether.
- the most preferable humectants are diethylene glycol, polyethylene glycol (200 to 600), triethylene glycol, ethylene glycol, glycerin and N-methyl-2-pyrrolidone, by which the solubility of the employed dye in the solvent of the ink composition can be increased and the evaporation of water from the ink composition can be appropriately controlled, so that the initial properties of the ink can be maintained even for an extended period of continuous use or storage, or during the periods when the apparatus is not in use, whereby reliable ink droplet stability and ink droplet ejection response of the ink, particularly after a prolonged period of non-use of the apparatus, are obtained.
- the above humectant be contained in an amount of 5 to 80 parts by weight, more preferably 10 to 40 parts by weight, with respect to 100 parts by weight of the ink composition according to the present invention, from the viewpoint of obtaining an appropriate viscosity and drying speed of the ink composition.
- additives for instance, water-soluble preservative and anti-mold agents, pH adjustment agents, specific electric conductivity adjustment agents, chelating agents and anti-rusting agents, can be added to the ink composition.
- water-soluble preservative and anti-mold agents for example, sodium dehydroacetate, sodium sorbate, 2-pyridine thiol-1-oxide sodium salt, sodium benzoate and sodium pentachlorophenol can be employed.
- any materials can be used optionally, so long as they do not have an adverse effect on the ink composition and can control the pH of the ink composition within the range of pH 9.0 to 11.0.
- pH adjustment agents are amines, such as diethanolamine and triethanolamine; hydroxides of alkali metals, such as lithium hydroxide, sodium hydroxide and potassium hydroxide; ammonium hydroxide; and carbonates of alkali metals, such as lithium carbonate, sodium carbonate and potassium carbonate.
- inorganic salts such as potassium chloride, ammonium chloride, sodium sulfate and sodium carbonate, and water-soluble amines such as triethanolamine can be employed.
- rust preventing agents for the nozzles for example, acid sulfites, sodium thiosulfate, ammonium thioglycolate, diisopropyl ammonium nitrite, pentaerythritol tetranitrate and dicyclohexyl ammonium nitrite can be employed.
- additives for example, water-soluble ultraviolet-ray-absorbing agents, water-soluble infrared-ray-absorbing agents, water-soluble polymeric compounds, solubility increasing agents for increasing the solubility of the dye dissolved in the solvent of the ink composition, and surfactants can be employed as thought necessary in specific embodiments of an aqueous ink composition for ink-jet recording according to the present invention.
- the ink composition was then subjected to the following tests: (1) Image Clarity and Image Dryness Test
- the ink composition was caused to issue from a nozzle with an inner diameter of 30 ⁇ m, with vibrations at a frequency of 100 KHz, by which vibrations the ink was ejected in a stream broken into individual drops, and was then caused to impinge on a sheet of commercially available high quality paper. As a result, clear images were obtained on each of the sheet.
- the time required for drying the printed image was not more than 10 seconds at normal room temperature and humidity.
- Example 1 was repeated except that the dye (1) employed in Example 1 was replaced by the dye (3) in Table 1, having the following formula, whereby an aqueous ink composition No. 2 for ink-jet recording according to the present invention was prepared: ##STR19##
- Example 1 was repeated except that the dye (1) employed in Example 1 was replaced by the dye (6) in Table 1, having the following formula, whereby an aqueous ink composition No. 3 for ink-jet recording according to the present invention was prepared: ##STR20##
- Example 1 was repeated except that the dye (1) employed in Example 1 was replaced by the dye (9) in Table 1, having the following formula, whereby an aqueous ink composition No. 4 for ink-jet recording according to the present invention was prepared: ##STR21##
- Example 1 was repeated except that the dye (1) employed in Example 1 was replaced by the dye (14) in Table 1, having the following formula, whereby an aqueous ink composition No. 5 for ink-jet recording according to the present invention was prepared: ##STR22##
- Example 1 was repeated except that the dye (1) employed in Example 1 was replaced by Acid Red 254, whereby a comparative aqueous ink composition for ink-jet recording was prepared.
- aqueous inks No. 2 through No. 5 according to the present invention and the comparative aqueous ink were also subjected to the same tests as in Example 1. The results were as follows:
Abstract
Description
TABLE 1 ______________________________________ ##STR5## (1) ##STR6## (2) ##STR7## (3) ##STR8## (4) ##STR9## (5) ##STR10## (6) ##STR11## (7) ##STR12## (8) ##STR13## (9) ##STR14## (10) ##STR15## (11) ##STR16## (12) ##STR17## (13) ##STR18## (14) ______________________________________
______________________________________ wt. % ______________________________________ Dye (1) in Table 1 3.0 Glycerin 5.0 Diethylene glycol 15.0 Sodium dehydroacetate 0.2 Ion-exchanged water 76.8 ______________________________________
TABLE 2 ______________________________________ Comparative Ex. 2 Ex. 3 Ex. 4 Ex. 5 Example ______________________________________ Image Clarity Clear Clear Clear Clear Nearly M M M R clear M Image Dryness <10 <10 <10 <10 <10 (seconds) Preservability Same Same Same Same Precipitates formed at 90° C. for 1 week Ink Droplet Same Same Same Same Ejecting Ejection direction Stability changed due to partial clogging Ink Droplet Same Same Same Same Unstable due Ejection to partial Response clogging in storage at 40° C. for 1 week ______________________________________
Claims (9)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59221275A JPS61101568A (en) | 1984-10-23 | 1984-10-23 | Water based ink |
JP59-221275 | 1984-10-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
US4631085A true US4631085A (en) | 1986-12-23 |
Family
ID=16764221
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/790,197 Expired - Fee Related US4631085A (en) | 1984-10-23 | 1985-10-22 | Aqueous ink composition for ink-jet recording |
Country Status (4)
Country | Link |
---|---|
US (1) | US4631085A (en) |
JP (1) | JPS61101568A (en) |
DE (1) | DE3537725A1 (en) |
GB (1) | GB2166145B (en) |
Cited By (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4761180A (en) * | 1986-08-27 | 1988-08-02 | Hewlett-Packard Company | Dyes containing tetramethylammonium cation for ink-jet printing inks |
US4765838A (en) * | 1985-08-13 | 1988-08-23 | Mitsubishi Chemical Industries Ltd. | Water-soluble dye composition and recording liquid containing the same |
US4786327A (en) * | 1986-09-29 | 1988-11-22 | Hewlett-Packard Company | Dye preparation for thermal ink-jet printheads using ion exchange |
US4994110A (en) * | 1986-08-27 | 1991-02-19 | Hewlett-Packard Company | Dyes containing lithium for ink-jet printing inks |
US5074914A (en) * | 1988-10-25 | 1991-12-24 | Canon Kabushiki Kaisha | Recording liquid and ink-jet recording method making use of it |
US5135571A (en) * | 1988-06-07 | 1992-08-04 | Canon Kabushiki Kaisha | Recording liquid |
US5254160A (en) * | 1992-12-14 | 1993-10-19 | Lexmark International, Inc. | Magenta dye, jet ink, and color set |
US5599386A (en) * | 1994-05-12 | 1997-02-04 | Mitsubishi Chemical Corporation | Recording liquid |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
US5709955A (en) | 1994-06-30 | 1998-01-20 | Kimberly-Clark Corporation | Adhesive composition curable upon exposure to radiation and applications therefor |
US5713992A (en) * | 1995-03-02 | 1998-02-03 | Mitsubishi Chemical Corporation | Recording liquid |
US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable dye compositions, and methods of developing a color |
US5837429A (en) | 1995-06-05 | 1998-11-17 | Kimberly-Clark Worldwide | Pre-dyes, pre-dye compositions, and methods of developing a color |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5858586A (en) | 1993-08-05 | 1999-01-12 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US5866638A (en) * | 1995-12-01 | 1999-02-02 | Canon Kabushiki Kaisha | Ink for two-part liquid system recording, and ink set, ink container, recording unit, recording process and recording apparatus using the same |
US5885337A (en) | 1995-11-28 | 1999-03-23 | Nohr; Ronald Sinclair | Colorant stabilizers |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6008268A (en) | 1994-10-21 | 1999-12-28 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition, method of generating a reactive species, and applications therefor |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US6033465A (en) | 1995-06-28 | 2000-03-07 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US6228157B1 (en) | 1998-07-20 | 2001-05-08 | Ronald S. Nohr | Ink jet ink compositions |
US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
US6265458B1 (en) | 1998-09-28 | 2001-07-24 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
US6368396B1 (en) | 1999-01-19 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
US6444020B1 (en) * | 1999-04-16 | 2002-09-03 | Fuji Photo Film Co., Ltd. | Tetraalkyl-substituted nitrogen-containing hetero ring-bonded azo dye, ink-jet ink comprising said dye, ink-jet recording method using said ink, and thermal transfer recording material comprising said dye |
US6486227B2 (en) | 2000-06-19 | 2002-11-26 | Kimberly-Clark Worldwide, Inc. | Zinc-complex photoinitiators and applications therefor |
US6503559B1 (en) | 1998-06-03 | 2003-01-07 | Kimberly-Clark Worldwide, Inc. | Neonanoplasts and microemulsion technology for inks and ink jet printing |
US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US20030037700A1 (en) * | 2001-08-02 | 2003-02-27 | Yi-Jing Leu | Highly bleed-alleviating ink composition |
US20030116056A1 (en) * | 2001-12-21 | 2003-06-26 | Benq Corporation | Multicolor dye set and inkjet ink composition with high chroma |
US20030127018A1 (en) * | 2001-12-25 | 2003-07-10 | Beno Corporation | Cyan dye set and ink-jet ink composition with high water-fastness |
US20030136299A1 (en) * | 2001-12-25 | 2003-07-24 | Beno Corporation | Inkjet ink composition with high chroma |
US6669766B2 (en) | 2001-07-13 | 2003-12-30 | Benq Corporation | Dye set and ink composition with high water-fastness |
US6730149B2 (en) | 2001-01-22 | 2004-05-04 | Ricoh Company Limited | Ink composition and inkjet recording method and apparatus using the ink composition |
US6786588B2 (en) * | 2001-03-23 | 2004-09-07 | Ricoh Company Limited | Pretreatment liquid for recording material and image recording method using the pretreatment liquid |
US20070197685A1 (en) * | 2006-01-18 | 2007-08-23 | Tamotsu Aruga | Recording ink as well as ink media set, ink cartridge, ink recorded matter, inkjet recording apparatus and inkjet recording method |
US7927416B2 (en) | 2006-10-31 | 2011-04-19 | Sensient Colors Inc. | Modified pigments and methods for making and using the same |
US7964033B2 (en) | 2007-08-23 | 2011-06-21 | Sensient Colors Llc | Self-dispersed pigments and methods for making and using the same |
US8708475B2 (en) | 2010-12-14 | 2014-04-29 | Ricoh Company, Ltd. | Ultraviolet crosslinking inkjet ink, ink cartridge containing same, and image forming method and apparatus using same |
US8727522B2 (en) | 2011-01-04 | 2014-05-20 | Ricoh Company, Ltd. | Ultraviolet crosslinking ink and inkjet recording method |
US8740374B2 (en) | 2011-03-25 | 2014-06-03 | Ricoh Company, Ltd. | Ink jet recording method, ink jet recording apparatus, and ink jet recorded matter |
US8807731B2 (en) | 2010-06-02 | 2014-08-19 | Ricoh Company, Ltd. | Inkjet image forming apparatus and inkjet image forming method |
US8815140B2 (en) | 2010-04-09 | 2014-08-26 | Ricoh Company, Ltd. | Method of producing film by inkjet process, and film |
US9221986B2 (en) | 2009-04-07 | 2015-12-29 | Sensient Colors Llc | Self-dispersing particles and methods for making and using the same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2779755A (en) * | 1951-04-25 | 1957-01-29 | Saul & Co | Cupriferous trisazo dyestuffs |
US4512807A (en) * | 1982-02-17 | 1985-04-23 | Fuji Photo Film Co., Ltd. | Aqueous ink composition for ink-jet printing |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56143275A (en) * | 1980-04-10 | 1981-11-07 | Canon Inc | Recording solution and method of recording |
JPS57174360A (en) * | 1981-04-20 | 1982-10-27 | Nippon Telegr & Teleph Corp <Ntt> | Ink composition |
JPS57174361A (en) * | 1981-04-21 | 1982-10-27 | Fujitsu Ltd | Ink for ink jet recording |
JPS5874760A (en) * | 1981-10-27 | 1983-05-06 | Fuji Photo Film Co Ltd | Water ink for ink jet printing |
JPS5925845A (en) * | 1982-08-05 | 1984-02-09 | Canon Inc | Recording liquid |
JPS5925854A (en) * | 1982-08-05 | 1984-02-09 | Canon Inc | Recording liquid |
-
1984
- 1984-10-23 JP JP59221275A patent/JPS61101568A/en active Pending
-
1985
- 1985-10-22 US US06/790,197 patent/US4631085A/en not_active Expired - Fee Related
- 1985-10-23 DE DE19853537725 patent/DE3537725A1/en active Granted
- 1985-10-23 GB GB8526167A patent/GB2166145B/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2779755A (en) * | 1951-04-25 | 1957-01-29 | Saul & Co | Cupriferous trisazo dyestuffs |
US4512807A (en) * | 1982-02-17 | 1985-04-23 | Fuji Photo Film Co., Ltd. | Aqueous ink composition for ink-jet printing |
Cited By (84)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4765838A (en) * | 1985-08-13 | 1988-08-23 | Mitsubishi Chemical Industries Ltd. | Water-soluble dye composition and recording liquid containing the same |
US4761180A (en) * | 1986-08-27 | 1988-08-02 | Hewlett-Packard Company | Dyes containing tetramethylammonium cation for ink-jet printing inks |
US4994110A (en) * | 1986-08-27 | 1991-02-19 | Hewlett-Packard Company | Dyes containing lithium for ink-jet printing inks |
US4786327A (en) * | 1986-09-29 | 1988-11-22 | Hewlett-Packard Company | Dye preparation for thermal ink-jet printheads using ion exchange |
US5135571A (en) * | 1988-06-07 | 1992-08-04 | Canon Kabushiki Kaisha | Recording liquid |
US5074914A (en) * | 1988-10-25 | 1991-12-24 | Canon Kabushiki Kaisha | Recording liquid and ink-jet recording method making use of it |
US5254160A (en) * | 1992-12-14 | 1993-10-19 | Lexmark International, Inc. | Magenta dye, jet ink, and color set |
US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
US6060200A (en) | 1993-08-05 | 2000-05-09 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms and methods |
US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
US6066439A (en) | 1993-08-05 | 2000-05-23 | Kimberly-Clark Worldwide, Inc. | Instrument for photoerasable marking |
US6060223A (en) | 1993-08-05 | 2000-05-09 | Kimberly-Clark Worldwide, Inc. | Plastic article for colored printing and method for printing on a colored plastic article |
US5908495A (en) | 1993-08-05 | 1999-06-01 | Nohr; Ronald Sinclair | Ink for ink jet printers |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US6127073A (en) | 1993-08-05 | 2000-10-03 | Kimberly-Clark Worldwide, Inc. | Method for concealing information and document for securely communicating concealed information |
US6054256A (en) | 1993-08-05 | 2000-04-25 | Kimberly-Clark Worldwide, Inc. | Method and apparatus for indicating ultraviolet light exposure |
US6120949A (en) | 1993-08-05 | 2000-09-19 | Kimberly-Clark Worldwide, Inc. | Photoerasable paint and method for using photoerasable paint |
US5858586A (en) | 1993-08-05 | 1999-01-12 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6342305B1 (en) | 1993-09-10 | 2002-01-29 | Kimberly-Clark Corporation | Colorants and colorant modifiers |
US5599386A (en) * | 1994-05-12 | 1997-02-04 | Mitsubishi Chemical Corporation | Recording liquid |
US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
US5709955A (en) | 1994-06-30 | 1998-01-20 | Kimberly-Clark Corporation | Adhesive composition curable upon exposure to radiation and applications therefor |
US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
US6090236A (en) | 1994-06-30 | 2000-07-18 | Kimberly-Clark Worldwide, Inc. | Photocuring, articles made by photocuring, and compositions for use in photocuring |
US6008268A (en) | 1994-10-21 | 1999-12-28 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition, method of generating a reactive species, and applications therefor |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US6235095B1 (en) | 1994-12-20 | 2001-05-22 | Ronald Sinclair Nohr | Ink for inkjet printers |
US5713992A (en) * | 1995-03-02 | 1998-02-03 | Mitsubishi Chemical Corporation | Recording liquid |
US5837429A (en) | 1995-06-05 | 1998-11-17 | Kimberly-Clark Worldwide | Pre-dyes, pre-dye compositions, and methods of developing a color |
US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable dye compositions, and methods of developing a color |
US6063551A (en) | 1995-06-05 | 2000-05-16 | Kimberly-Clark Worldwide, Inc. | Mutable dye composition and method of developing a color |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US6033465A (en) | 1995-06-28 | 2000-03-07 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US5885337A (en) | 1995-11-28 | 1999-03-23 | Nohr; Ronald Sinclair | Colorant stabilizers |
US6168655B1 (en) | 1995-11-28 | 2001-01-02 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5866638A (en) * | 1995-12-01 | 1999-02-02 | Canon Kabushiki Kaisha | Ink for two-part liquid system recording, and ink set, ink container, recording unit, recording process and recording apparatus using the same |
US6168654B1 (en) | 1996-03-29 | 2001-01-02 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6503559B1 (en) | 1998-06-03 | 2003-01-07 | Kimberly-Clark Worldwide, Inc. | Neonanoplasts and microemulsion technology for inks and ink jet printing |
US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6228157B1 (en) | 1998-07-20 | 2001-05-08 | Ronald S. Nohr | Ink jet ink compositions |
US6265458B1 (en) | 1998-09-28 | 2001-07-24 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6368396B1 (en) | 1999-01-19 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
US6444020B1 (en) * | 1999-04-16 | 2002-09-03 | Fuji Photo Film Co., Ltd. | Tetraalkyl-substituted nitrogen-containing hetero ring-bonded azo dye, ink-jet ink comprising said dye, ink-jet recording method using said ink, and thermal transfer recording material comprising said dye |
US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
US6486227B2 (en) | 2000-06-19 | 2002-11-26 | Kimberly-Clark Worldwide, Inc. | Zinc-complex photoinitiators and applications therefor |
US6918662B2 (en) | 2001-01-22 | 2005-07-19 | Ricoh Company Limited | Ink composition and inkjet recording method and apparatus using the ink composition |
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US6786588B2 (en) * | 2001-03-23 | 2004-09-07 | Ricoh Company Limited | Pretreatment liquid for recording material and image recording method using the pretreatment liquid |
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US20050007431A1 (en) * | 2001-03-23 | 2005-01-13 | Masayuki Koyano | Pretreatment liquid for recording material and image recording method using the pretreatment liquid |
US6669766B2 (en) | 2001-07-13 | 2003-12-30 | Benq Corporation | Dye set and ink composition with high water-fastness |
US6899753B2 (en) | 2001-08-02 | 2005-05-31 | Benq Corporation | Highly bleed-alleviating ink composition |
US20030037700A1 (en) * | 2001-08-02 | 2003-02-27 | Yi-Jing Leu | Highly bleed-alleviating ink composition |
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US20030127018A1 (en) * | 2001-12-25 | 2003-07-10 | Beno Corporation | Cyan dye set and ink-jet ink composition with high water-fastness |
US6793722B2 (en) | 2001-12-25 | 2004-09-21 | Benq Corporation | Inkjet ink composition with high chroma |
US20030136299A1 (en) * | 2001-12-25 | 2003-07-24 | Beno Corporation | Inkjet ink composition with high chroma |
US20070197685A1 (en) * | 2006-01-18 | 2007-08-23 | Tamotsu Aruga | Recording ink as well as ink media set, ink cartridge, ink recorded matter, inkjet recording apparatus and inkjet recording method |
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US8740374B2 (en) | 2011-03-25 | 2014-06-03 | Ricoh Company, Ltd. | Ink jet recording method, ink jet recording apparatus, and ink jet recorded matter |
Also Published As
Publication number | Publication date |
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GB2166145B (en) | 1988-06-29 |
DE3537725C2 (en) | 1988-08-04 |
GB2166145A (en) | 1986-04-30 |
DE3537725A1 (en) | 1986-04-24 |
GB8526167D0 (en) | 1985-11-27 |
JPS61101568A (en) | 1986-05-20 |
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